A Copper(I)-Catalyzed Enantioselective γ-Boryl Substitution of Trifluoromethyl-Substituted Alkenes: Synthesis of Enantioenriched γ,γ-gem-Difluoroallylboronates.

Angew Chem Int Ed Engl

Division of Applied Chemistry and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido, 060-8628, Japan.

Published: June 2018

The first catalytic enantioselective γ-boryl substitution of CF -substituted alkenes is reported. A series of CF -substituted alkenes was treated with a diboron reagent in the presence of a copper(I)/Josiphos catalyst to afford the corresponding optically active γ,γ-gem-difluoroallylboronates in high enantioselectivity. The thus obtained products could be readily converted into the corresponding difluoromethylene-containing homoallylic alcohols using highly stereospecific allylation reactions.

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http://dx.doi.org/10.1002/anie.201803663DOI Listing

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